sodium (16S,20S)-16,20-dihydroxy-19-norergosta-1,3,5(10),24(28)-tetraen-3-yl sulfate

ID: ALA1079368

PubChem CID: 44254700

Max Phase: Preclinical

Molecular Formula: C27H39NaO6S

Molecular Weight: 492.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(CC[C@](C)(O)[C@H]1[C@@H](O)C[C@H]2[C@@H]3CCc4cc(OS(=O)(=O)[O-])ccc4[C@H]3CC[C@@]21C)C(C)C.[Na+]

Standard InChI:  InChI=1S/C27H40O6S.Na/c1-16(2)17(3)10-13-27(5,29)25-24(28)15-23-22-8-6-18-14-19(33-34(30,31)32)7-9-20(18)21(22)11-12-26(23,25)4;/h7,9,14,16,21-25,28-29H,3,6,8,10-13,15H2,1-2,4-5H3,(H,30,31,32);/q;+1/p-1/t21-,22-,23+,24+,25+,26+,27+;/m1./s1

Standard InChI Key:  NEUXUTVGTQPWGU-FFRRAXGHSA-M

Molfile:  

     RDKit          2D

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    4.0086   -9.5949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7204  -10.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4320   -9.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.3505   -8.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  6 10  1  0
  3 19  1  0
  7  8  1  0
 19 20  1  0
  8  9  1  0
 20 21  1  0
  9 11  1  0
 20 22  2  0
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  4  7  2  0
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  6  5  2  0
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  2  3  2  0
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  3  4  1  0
 17 37  1  1
 15 16  1  0
 18 38  1  6
 16 17  1  0
 14 39  1  1
 17 18  1  0
M  CHG  2   1   1  21  -1
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 492.68

Molecular Weight (Monoisotopic): 492.2546

AlogP: 5.05

#Rotatable Bonds: 7

Polar Surface Area: 104.06

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: -1.75

CX Basic pKa: ┄

CX LogP: 3.20

CX LogD: 2.49

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.36

Np Likeness Score: 2.26

References

1. Digirolamo JA, Li XC, Jacob MR, Clark AM, Ferreira D..  (2009)  Reversal of fluconazole resistance by sulfated sterols from the marine sponge Topsentia sp.,  72  (8): [PMID:19653640] [10.1021/np900177m]

Source

Source(1):

• Scientific Literature